Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/70—One oxygen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

• the cyclization of the amides (II) can e.g. with phosphorus pentachloride, advantageously in the presence of a solvent which is inert under the reaction conditions.
• a solvent which is inert under the reaction conditions. Examples of the latter are: toluene, xylene, chloroform or phosphorus oxychloride.
• the reaction temperature is not critical and can be varied between -10 ° C and + 150 ° C. Reaction temperatures between 0 and 100 ° C. are particularly advantageous.
• the hydrochlorides of the imidazolinones (I) are primarily obtained. According to usual methods, e.g. by reaction with sodium carbonate or sodium hydrogen carbonate, the free bases can be produced therefrom.
• the cyclization can also take place in the presence of strong organic or inorganic acids, such as sulfuric acid or p-toluenesulfonic acid, with simultaneous removal of the water formed at temperatures from 0 ° C. to 150 ° C.
• the reaction can be carried out particularly advantageously in such a way that the water formed is separated off by azeotropic distillation with a solvent such as toluene, xylene or chloroform. After neutralization, the products can be isolated using customary methods.
• the compounds according to the invention are tautomeric, so that they can be in one of the two forms (I a) / (I b) or as a mixture of (I a) and (I b). These isomers also occur in the derivatives with Z ⁇ H.
• Both the acid addition salts and the N-oxides of the compounds of the formula (I) are readily accessible in a generally known manner, the latter, for example, by reaction with peroxides or H 2 O 2 .
• the amides of the formula (II) can easily be obtained from the aminoamides (III) and the correspondingly substituted carboxylic acid derivatives (IV).
• the present compounds according to the invention have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants. Perennial root weeds that are difficult to control are also well captured by the active ingredients. It does not matter whether the substances are applied in pre-sowing, pre-emergence or post-emergence spraying. If the compounds according to the invention are applied to the earth's surface before germination, the emergence of the seedlings is not completely prevented. The weeds grow to the cotyledon stage, but then stop growing and eventually die completely after 3 weeks.
• the active ingredients When the active ingredients are applied to the green parts of the plant in the post-emergence process, there is also a drastic growth stop very quickly after the treatment and the weed plants remain in the growth stage at the time of application or die completely after a certain time, so that one for the crop plants U harmful nkrautkonkurrenz very early and can be permanently eliminated through the use of new compositions of the invention.
• the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledon weeds, crop plants of economically important crops such as, for. B. wheat, barley, rye, rice, maize, sugar beet, cotton and soy only insignificantly or even not harmed.
• the substances according to the invention thus have excellent selectivity in crop plants and, for these reasons, are very suitable for controlling unwanted vegetation in agricultural crops.
• the present invention therefore also relates to herbicidal and growth-regulating compositions which comprise the active compound of the formula (I) in addition to customary formulation auxiliaries.
• the agents according to the invention can be used as wettable powders, emulsifiable concentrates, sprayable solutions, dusts, mordants, dispersions, granules or microgranules in the usual preparations.
• Wettable powders are preparations which are uniformly dispersible in water and which, in addition to the active ingredient, in addition to, if appropriate, a diluent or inert substance, are also wetting agents, for.
• ligninsulfonic acid sodium 2,2'-di-naphthylmethane-6,6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or oleoylmethyl tauric acid sodium.
• the production takes place in the usual way, for. B. by grinding and mixing the components.
• Emulsifiable concentrates can e.g. B. by dissolving the active ingredient in an inert organic solvent, e.g. Example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or K ohlenwasserstof- fen with addition of one or more emulsifiers her.- are provided.
• an inert organic solvent e.g. Example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or K ohlenwasserstof- fen with addition of one or more emulsifiers her.- are provided.
• the solvent content can also be omitted entirely or in part.
• alkyl-arylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers
• alkyl-arylsulfonic acid calcium salts such as Ca-dodecylbenzenesulfonate or nonionic emulsifiers
• fatty acid polyglycol esters alkyl aryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, fatty alcohol propylene oxide or ethylene oxide polyorbityl ester polyorbityl acid fatty acid products, ethylene oxide polyorbityl ester fatty acid products, ethylene oxide polyorbityl ester fatty acid products, ethylene oxide polyorbityl ester fatty acid products, ethylene oxide polyorbityl ester fatty acid products, ethylene oxide polyorbityl ester fatty acid products, ethylene oxide polyorbityl ester fatty acid products, ethylene oxide
• Dusts can be obtained by grinding the active ingredient with finely divided, solid substances, e.g. B. talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
• finely divided, solid substances e.g. B. talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
• Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of binders, e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils on the surface of carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
• binders e.g. As polyvinyl alcohol, sodium polyacrylic acid or mineral oils on the surface of carriers such as sand, kaolinite or granulated inert material.
• Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
• the active ingredient concentration in wettable powders is e.g. B. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be approximately 10 to 80% by weight. Dust-like formulations usually contain 5 to 20 wt .-% of active ingredient, sprayable solutions about 2 to 20 wt .-%. In the case of granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulation aids, fillers, etc. are used.
• the active ingredient formulations mentioned optionally contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers.
• the concentrates present in the commercial form are optionally diluted in a conventional manner, for. B. with wettable powders, emulsifiable concentrates, dispersions and sometimes also with microgranules using water. Dusty and granular Preparations and sprayable solutions are usually no longer diluted with other inert substances before use.
• the application rates of active ingredient of the formula (I) vary, depending on the indication, between 0.01 and 10 kg of active ingredient / ha.
• a wettable powder which is readily dispersible in water is obtained by mixing 25 parts by weight of active compound, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of lignosulfonic acid potassium and 1 part by weight of oleoylmethyl tauric acid sodium as wetting and dispersing agent and grinding in a pin mill.
• a dispersion concentrate which is readily dispersible in water is obtained by mixing 20 parts by weight of active compound with 6 parts by weight of alkylphenol polyglycol ether (for example (R) Triton X 207 from Rohm & Haas Co.), 3 parts by weight.
• alkylphenol polyglycol ether for example (R) Triton X 207 from Rohm & Haas Co.
• An emulsifiable concentrate is obtained from 15 parts by weight of active ingredient, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethylated nonylphenol (10 AeO) as an emulsifier.
• Seeds or rhizome pieces of mono- and dicotyledon weeds were placed in clay soil in plastic pots (0 9 cm) and covered with soil.
• the mulsionskonzentrate as wettable powders or as E formulated compounds of the invention were applied as aqueous suspensions or emulsions on the surface.
• the amount of water applied per pot corresponded to the equivalent of 600 1 / ha.
• the test pots were placed in the greenhouse and the test plants were cultivated under good growth conditions (temperature: 23 ⁇ 1 ° C; relative humidity 60-80%). After approximately 3 weeks, the damage to the plants was assessed visually. Untreated controls served as a comparison.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)
• Plural Heterocyclic Compounds (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Applications Claiming Priority (2)

Publications (2)

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ID=6213909

Family Applications (1)

Country Status (14)

Cited By (6)

Families Citing this family (13)

Family Cites Families (4)

• 1983
  • 1983-11-10 DE DE19833340595 patent/DE3340595A1/de not_active Withdrawn
• 1984
  • 1984-11-02 HU HU844076A patent/HUT36341A/hu unknown
  • 1984-11-03 EP EP84113259A patent/EP0144748A3/fr not_active Withdrawn
  • 1984-11-08 PH PH31423A patent/PH20098A/en unknown
  • 1984-11-08 DD DD84269265A patent/DD231481A5/de unknown
  • 1984-11-08 US US06/669,620 patent/US4614535A/en not_active Expired - Fee Related
  • 1984-11-08 ES ES537502A patent/ES537502A0/es active Granted
  • 1984-11-09 AU AU35288/84A patent/AU3528884A/en not_active Abandoned
  • 1984-11-09 BR BR8405750A patent/BR8405750A/pt unknown
  • 1984-11-09 ZA ZA848760A patent/ZA848760B/xx unknown
  • 1984-11-09 KR KR1019840007012A patent/KR850003722A/ko not_active Withdrawn
  • 1984-11-09 IL IL73470A patent/IL73470A0/xx unknown
  • 1984-11-09 JP JP59235343A patent/JPS60123475A/ja active Pending
• 1985
  • 1985-04-01 CN CN198585101424A patent/CN85101424A/zh active Pending

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